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> Europe
> Italy
> Tuscany
> Province of Grosseto
> Roccastrada

Vacation homes - vacation rentals

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$1 $750 -

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  • Cottage (32)
  • Apartment (476)
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  • Penthouse (3)
  • Chalet (1)
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  • Bungalow (1)
  • Barn (4)
  • Townhouse (20)
  • Farmhouse (98)
  • Studio (11)
  • Yacht (1)
  • Chateau (1)
  • Finca (3)
  • Condo (2)
  • Tower (1)
  • Private room (3)
  • B&B (30)
  • Hotel apartment (31)
  • Guest house (4)

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32 Vacation rentals

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Cottage

Great rentals within 20 miles that match your search

Scansano Vacation cottage rental

Scansano cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6
1 review

from $111 / night

$798 - $1,314 / week

1 / 14

Great rentals within 20 miles that match your search

Vacation cottage in Val di Merse

Val di Merse cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Pricing unknown

1 / 13

Great rentals within 20 miles that match your search

Vacation cottage with swimming pool in Volterra

Volterra cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5
24 reviews

from $270 / night

$1,890 / week

1 / 35

Great rentals within 20 miles that match your search

Vacation cottage in Colle di Val d'Elsa

Colle di Val d'Elsa cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $137 / night

$959 / week

1 / 46

Great rentals within 20 miles that match your search

Vacation cottage rental

Colle di Val d'Elsa cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $141 / night

$985 / week

1 / 49

Great rentals within 20 miles that match your search

Vacation cottage in Colle di Val d'Elsa

Colle di Val d'Elsa cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $110 / night

$771 / week

1 / 46

Great rentals within 20 miles that match your search

Vacation cottage in Colle di Val d'Elsa

Colle di Val d'Elsa cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $110 / night

$771 / week

1 / 38

Great rentals within 20 miles that match your search

Vacation cottage in Colle di Val d'Elsa

Colle di Val d'Elsa cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $103 / night

$719 / week

1 / 43

Great rentals within 20 miles that match your search

Vacation cottage in Colle di Val d'Elsa

Colle di Val d'Elsa cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $110 / night

$771 / week

1 / 41

Great rentals within 20 miles that match your search

Vacation cottage rental

Colle di Val d'Elsa cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $103 / night

$719 / week

1 / 46

Great rentals within 20 miles that match your search

Vacation cottage in Colle di Val d'Elsa

Colle di Val d'Elsa cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $84 / night

$582 / week

1 / 39

Great rentals within 20 miles that match your search

Vacation cottage rental

Colle di Val d'Elsa cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $84 / night

$582 / week

1 / 40

Great rentals within 20 miles that match your search

Vacation cottage rental

Colle di Val d'Elsa cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $84 / night

$582 / week

1 / 39

Great rentals within 20 miles that match your search

Vacation cottage in Colle di Val d'Elsa

Colle di Val d'Elsa cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $81 / night

$565 / week

1 / 43

Great rentals within 20 miles that match your search

Vacation cottage with shared pool in Volterra

Volterra cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $79 / night

$393 / week

1 / 13

Great rentals within 20 miles that match your search

Civitella Paganico Vacation cottage rental

Civitella Paganico cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $744 / night

$5,204 / week

1 / 51

Great rentals within 20 miles that match your search

Cottage rental in Pievescola

Pievescola cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $234 / night

$1,633 / week

1 / 100

Great rentals within 20 miles that match your search

Cottage rental in Pievescola with shared pool

Pievescola cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $234 / night

$1,633 / week

1 / 62

Great rentals within 20 miles that match your search

Cottage rental in Pievescola with shared pool

Pievescola cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $234 / night

$1,633 / week

1 / 100

Great rentals within 20 miles that match your search

Pievescola Vacation cottage rental

Pievescola cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $307 / night

$2,148 / week

1 / 86

Great rentals within 20 miles that match your search

Cottage rental in Pievescola with shared pool

Pievescola cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $307 / night

$2,148 / week

1 / 91

Great rentals within 20 miles that match your search

Vacation cottage in Civitella Paganico

Civitella Paganico cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $105 / night

$657 / week

1 / 14

Great rentals within 20 miles that match your search

Cottage rental in Pievescola with shared pool

Pievescola cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $735 / night

$5,144 / week

1 / 70

Great rentals within 20 miles that match your search

Cottage rental in Pievescola with shared pool

Pievescola cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $234 / night

$1,633 / week

1 / 100

Great rentals within 20 miles that match your search

Cottage rental in Pievescola with shared pool

Pievescola cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $233 / night

$1,629 / week

1 / 100

Great rentals within 20 miles that match your search

Vacation cottage in Castel San Gimignano

Castel San Gimignano cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3
1 review

from $135 / night

$945 / week

1 / 28

Great rentals within 20 miles that match your search

Vacation cottage accommodation

Crete Senesi cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Pricing unknown

1 / 18

Great rentals within 20 miles that match your search

Cottage rental in Monteriggioni

Monteriggioni cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5
3 reviews

from $111 / night

$614 / week

1 / 28

Great rentals within 20 miles that match your search

Vacation cottage with shared pool in Scansano

Scansano cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2
1 review

from $74 / night

$516 / week

1 / 8

Great rentals within 20 miles that match your search

Vacation cottage with swimming pool, golf nearby in Casole d'Elsa

Casole d'Elsa cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6
18 reviews

from $228 / night

$1,590 / week

1 / 24

Great rentals within 20 miles that match your search

Volterra Vacation cottage rental

Volterra cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6
1 review

from $93 / night

$579 / week

1 / 5

Great rentals within 20 miles that match your search

Cottage rental in Monteguidi with swimming pool

Monteguidi cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
23 reviews

from $245 / night

$1,712 / week

1 / 29

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